1,1-Dichloroethane → 6-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one

HRID 988971Notes

Reaction equation

HRID 988971 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.O=S(Cl)Cl.Cl[CH:17](Cl)[CH3:18]>>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[CH2:8][C:9](=[O:11])[CH2:18][CH2:17]2

Participants

4

Reactant 3

HCID 63651,1-DichloroethaneHCID 98372-(4-Fluorophenyl)acetic acidHCID 24386Thionyl Chloride

Product 1

HCID 50443856-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one

Conditions

Temperature
0 °C

Procedure

4-fluorophenylacetic acid (1 equivalent) was dissolved in dichloroethane (1.3 M) containing SOCl2 (3 equivalents), the mixture was refluxed for 90 minutes and the solvent was removed. Solution of this crude product in CH2Cl2 was added dropwise within 60 minutes to AICl3 (2 eq) in CH2Cl2 (0.4 M) while stirring at 0° C. Thereafter, ethylene was introduced at 0° C. over 45 minutes, whereupon the mixture was stirred further at room temperature for 1 hour, and thereafter was treated at 0° C. with ice-water. The organic phase was washed with 1N HCl (2×), NaHCO3 (sat. sol.), dried and evaporated. The residue was triturated with hexane, yielding the product as a bright yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 90 minutes
  2. customthe solvent was removed
  3. additionSolution of this crude product in CH2Cl2 was added dropwise within 60 minutes to AICl3 (2 eq) in CH2Cl2 (0.4 M)
  4. additionThereafter, ethylene was introduced at 0° C. over 45 minutes, whereupon the mixture
  5. stirringwas stirred further at room temperature for 1 hour
  6. additionwas treated at 0° C. with ice-water
  7. washThe organic phase was washed with 1N HCl (2×), NaHCO3 (sat. sol.)
  8. customdried
  9. customevaporated
  10. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-00655fa07363462a8ee0f3464f6837a1
Source dataset
uspto-grants-2003_10
Patent number
US06638927B2

Reaction notes

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